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Structural chemistry and anti-inflammatory activity of flexible/restricted phenyl dimers

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Abstract

Three phenyl dimer compounds, namely 3,3′-Diformyldiphenoxyethane (C16H14O4) (1), 1-(4-[2-(4-Acetyl-phenoxy)-ethoxy]-phenyl)-ethanone (C17H16N2O3) (2), 1-{4-[2-(4-Acetyl-phenoxymethyl)-benzyloxy]-phenyl}-ethanone (C24H22O4) (3), were obtained and fully characterized, including their crystal structure determinations. The structural properties of two compounds 4, 4′-(ethylenedioxy)dibenzaldehyde) (C16H14O4) (Tewari et al. Acta Cryst. E63:o1930, 2007) [1] (4) and 4-(2-Phenoxy-ethoxy)-benzaldehyde (C15H14O3) (Valgera et al. CCDC 710835, 2016) [2] (5) are discussed with the role of the substituent in crystal packing. In vivo, anti-inflammatory activities of all compounds were studied on Wistar strain albino rats. All the compounds exhibited anti-inflammatory activity except 5. Compounds 1, 2, 4 have shown moderate-to-intermediate effects on inhibitory properties. Compound (3) with restricted rotation in the compound-like SC-558 drug was shown to possess good inhibitory properties at 180 min. In silico analysis was performed and compared with experimental in vivo results.

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References

  1. A.K. Tewari, V.P. Singh, M.C. Puerta, P. Valerga, Acta Cryst. E63, o1930 (2007)

    Google Scholar 

  2. P. Valerga, M.C. Puerta, CCDC 710835: Experimental Crystal Structure Determination (2016). https://doi.org/10.5517/ccdc.csd.ccrvp5f

  3. D.P. Marriott, I.G. Dougall, P. Meghani, Y.J. Liu, D.R. Flower, J. Med. Chem. 42, 3210 (1999)

    Article  CAS  Google Scholar 

  4. C.A. Hunter, Chem. Soc. Rev. 23, 101 (1994)

    Article  CAS  Google Scholar 

  5. R. Glaser, L.R. Dendi, N. Knotts, C.L. Barnes, Cryst. Growth Des. 3, 291 (2003)

    Article  CAS  Google Scholar 

  6. A.K. Tewari, P. Srivastava, M.C. Puerta, P. Valerga, J. Mol. Struct. 921, 251 (2009)

    Article  CAS  Google Scholar 

  7. R. Dubey, A.K. Tewari, K. Ravikumar, B. Sridhar, J. Chem. Crystallogr. 41, 886 (2011)

    Article  CAS  Google Scholar 

  8. P. Srivastava, V.P. Singh, A.K. Tewari, C. Puerta, P. Valerga, J. Mol. Struct. 1007, 20 (2012)

    Article  CAS  Google Scholar 

  9. M.R. Yadav, S.T. Shirude, A. Parmar, R. Balaraman, R. Giridhar, Chem. Heterocycl. Compd. 42, 8 (2006)

    Article  Google Scholar 

  10. K.R.A. Abdellatif, M.A. Chowdhury, Y. Dong, D. Das, G. Yu, C.A. Velázquez, M.R. Suresh, E.E. Knaus, Bioorg. Med. Chem. Lett. 19(11), 3014 (2009)

    Article  CAS  Google Scholar 

  11. M.H. Yang, K.D. Yoon, Y.W. Chin, J.H. Park, J. Kim, Bioorg. Med. Chem. 17(7), 2689 (2009)

    Article  CAS  Google Scholar 

  12. S.K. Rai, S. Khanam, R.S. Khanna, A.K. Tewari, Cryst. Growth Des. 15, 1430 (2015)

    Article  CAS  Google Scholar 

  13. A. Zarghi, S. Arfaei, Iran. J. Pharm. Res. 10(4), 655 (2011)

    CAS  PubMed  PubMed Central  Google Scholar 

  14. A. Palomer, F. Cabre, J. Pascual, J. Campos, M.A. Trujillo, A. Entrena, M.A. Gallo, L. García, D. Mauleón, A. Espinosa, J. Med. Chem. 45(7), 1402 (2002)

    Article  CAS  Google Scholar 

  15. M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka and M. A. Spackman, CrystalExplorer17. (2017) http://crystalexplorer.scb.uwa.edu.au. Accessed 2 Apr 2019

  16. S.F. Boys, F. Bernardi, Mol. Phys. 19, 553 (1970)

    Article  CAS  Google Scholar 

  17. M.J. Turner, S. Grabowsky, D. Jayatilaka, M.A. Spackman, J. Phys. Chem. Lett. 5, 4249 (2014)

    Article  CAS  Google Scholar 

  18. C.F. Mackenzie, P.R. Spackman, D. Jayatilaka, M.A. Spackman, IUCrJ 4, 575 (2017)

    Article  CAS  Google Scholar 

  19. F.H. Allen, D.G. Watson, L. Brammer, A.G. Orpen, R. Taylor, in International Tables for Crystallography, 3rd edn., ed. by E. Prince (Springer, Heidelberg, 2004), pp. 790–811

    Google Scholar 

  20. A.L. Spek, Acta Cryst. D65, 148 (2009)

    Google Scholar 

  21. Bruker, APEX2, SAINT and SADABS (Bruker AXS Inc., Madison, 2015)

    Google Scholar 

  22. G.M. Sheldrick, Acta Cryst. A71, 3 (2015)

    Google Scholar 

  23. S.P. Westrip, J. Appl. Cryst. 43, 920 (2010)

    Article  CAS  Google Scholar 

  24. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Glidehans, J.M. Miyashiro, T.D. Penning, K. Seibert, P.C. Isakson, W.C. Stallings, Nature 384, 644 (1996)

    Article  CAS  Google Scholar 

  25. C.A. Wintar, E.A. Risley, G.W. Nuss, Proc. Soc. Exp. Biol. 111, 544 (1962)

    Article  Google Scholar 

  26. A.K. Tewari, P. Srivastawa, V.P. Singh, A. Singh, R.K. Goel, C.G. Mohan, Chem. Pharm. Bull. 58(5), 634 (2010)

    Article  CAS  Google Scholar 

  27. R. Thakuria, N.K. Nath, B.K. Saha, Cryst. Growth Des. 19, 523 (2019)

    Article  CAS  Google Scholar 

  28. A. Banerjee, A. Saha, B.K. Saha, Cryst. Growth Des. 19, 2245 (2019)

    Article  CAS  Google Scholar 

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Acknowledgements

Department of Chemistry, Banaras Hindu University, Varanasi, India, is acknowledged for departmental facilities. Department of Chemistry, Mizoram University, Aizawl, Mizoram, India, is acknowledged the other infrastructure facilities. SAIF, Gauhati University, Guwahati, India, is acknowledged for SCXRD facilities. Institute of Medical Sciences, B.H.U, Varanasi, India, is acknowledged for providing the space and facilities to perform biological analysis. Jayanta Dowarah acknowledges DST, New Delhi, for DST-inspired fellowship.

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Authors and Affiliations

  1. Department of Chemistry, School of Physical Sciences, Mizoram University, Aizawl, 796004, India

    Ved Prakash Singh & Jayanta Dowarah

  2. Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi, 221005, India

    Ashish Kumar Tewari

  3. Department of Chemistry, College of Genesco, State University of New York, Genesco, NY, 4454, USA

    David K. Geiger

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  1. Ved Prakash Singh
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  2. Jayanta Dowarah
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  3. Ashish Kumar Tewari
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  4. David K. Geiger
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Correspondence to Ved Prakash Singh or Ashish Kumar Tewari.

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Singh, V.P., Dowarah, J., Tewari, A.K. et al. Structural chemistry and anti-inflammatory activity of flexible/restricted phenyl dimers. J IRAN CHEM SOC 17, 1289–1303 (2020). https://doi.org/10.1007/s13738-020-01853-x

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